


Briar Stiles (Or Five Times Stiles got Fucked by Werewolves while Sleeping, and Five Times when he was Awake)

by ClassiqueMystique



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Barebacking, Blindfolds, Bottom Stiles Stilinski, Coming Untouched, Consensual Somnophilia, Crossdressing Kink, Daddy Kink, Dirty Talk, Double Anal Penetration, Each Wolf Has A Kink, Feathers & Featherplay, Fucking Machines, Implied/Referenced Incest, Japanese Silk Rope, Lipstick, Locker Room Sex, M/M, Marking, NSFW Art, Pack Whore Stiles, Plot What Plot/Porn Without Plot, Rimming, Rough Sex, Sex Toys, Shibari Rope Style Bondage, Slight Cock Wrapping, Slight feminization, Slut Shaming, Underage-Stiles is 17, Voyeurism, Werewolf Healing, drabble style, ice cubes, illustrator mentioned in notes below, picture not mine, pseudo- first time, pseudo- virgin/ity, roleplay kink
Language: English
Status: In-Progress
Published: 2014-03-16
Updated: 2016-11-14
Packaged: 2018-01-15 21:36:13
Rating: Explicit
Warnings: Underage
Chapters: 14
Words: 17,223
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1320031
Author URL: https://archiveofourown.org/users/ClassiqueMystique/pseuds/ClassiqueMystique
Summary: <blockquote class="userstuff">
              <p>Stiles said he would do all he can to help his pack. And he meant it…in every way required.</p><p>11/13/16: I've added another new chapter. The pairing this time is Stisaac. Enjoy!<br/>Please read the notes before proceeding, just in case.</p>
            </blockquote>





	1. Let the Fun Begin

**1**

 

Stiles remembered the day he attended his first pack meeting. Derek had called him on his cell and told him to be at the loft by seven. Never said what it was concerning, but Stiles didn’t care. He drove all the way to Derek’s with a smile on his face. _Finally_ , he had thought. The others consistently pestered him to help with research to solve their problems in the past, and Scott always needed help with something werewolf related, or Allison related. The latter probably frustrated Stiles the most. But never before had he been asked to go to the official pack meetings. Never before had they wanted to include him.

 

When he got there, he was surrounded by the warm contented smiles on everyone’s face, even Derek’s. The latter nearly being a source of a heart attack for him. And the whole gang was there: Derek, Isaac, Jackson, Lydia, Scott, Allison, and Peter. They immersed him immediately into their conversation, thanking him for all he’s done, making him feel welcomed and wanted. It was like a dream come true for the teen—his own personal rite of passage into this exclusive family. He embraced everything with open arms. So that’s why, when the meeting was over and Derek approached him to quietly pose the question “How far would you go to help your pack mates,” Stiles responded; “I’ll do whatever is required of me.” Those were words he would never forget, or regret.

 

And as he stood in front of his mirror, dressed only in an over sized t-shirt, the light of the moon bathing him in her glow, he smiled. “Let the fun begin.”

TBC....


	2. When the Princess Sleeps: Encounter With an Alpha

**2**

 

The nighttime visits didn’t start right away. It took almost two months since his first pack meeting before the first werewolf crept into his bedroom through his window one night. Then one by one, they all did. Somehow, they all coordinated their visits so that no one’s overlapped. At least that’s what Stiles believed, even though he had no way of being truly certain. Because whenever a wolf came to him, he was always asleep, and Stiles could sleep like the dead. In fact, his mom used to call him Briar Stiles, after the fairy tale Briar Rose, or Sleeping Beauty. No amount of yelling, hitting or horseplay would be enough to wake Stiles up when he went under. In fact, he slept right through an earthquake onetime years ago, never once hearing one of the trees outside his window fall over onto the house and crash into his bedroom. So naturally, the first werewolf—the Alpha of Beacon Hills—was able to come and go with no problem. And Stiles had no problem with that.

 

Derek visited just after the full moon of March. At least Stiles was pretty sure it was Derek. Every one of his wolves had their own signature—every one of them left clues behind which Stiles used to identify who had fucked him the night prior. He never said anything to any of them while he was awake, of course. But in his mind, he could tell when his body had had some quality time with Derek. When conscious, Stiles noticed that Derek seemed to be the only one near bursting with a combination of pent up energy, anger and sexual frustration. So he figured that the finger-shaped bruises on his shoulders and hips had to have been Derek’s doing. He must have needed desperate release. The thought alone made the teen hard one morning as he brushed the tips of his fingers over the rim of his sore hole. He moaned at the idea that Derek came through his only window last night, his huge cock straining against the seam of his jeans. Stiles wished he could have seen the Alpha’s face when he saw his prey asleep belly down, naked, and with his ass high in the air. Stiles glanced at his fingers, smiling when he noticed them glisten in the early morning light—a mixture of lube and cum. _Lots of cum._ He wondered if Derek was pleased when first touched Stiles, noticing that the teen had prepped himself. Did he think about it—did he try to picture it? Did he imagine Stiles lying in the middle of his bed, knees bent to his shoulders with three fingers pumping in and out of his hole? Did he wish he were there to watch?

 

Stiles bypassed his cock, running his hands over his hairless balls. He was surprised but even more excited to feel two thin lines of curved bumps spanning almost the entire length. He didn’t need a mirror to know what it was. _Teeth._ And to be even more specific, _zipper teeth_. The thought filled Stiles with glee. Derek couldn’t even wait to take his jeans off before he fucked him rough—rough enough to leave an imprint. An imprint that should have faded a while ago if the Alpha arrived in the dead of night. Stiles glanced at his bedside clock, the red letters reflecting **5:06am.** He moaned as he slipped his fingers inside, whimpering at the feel of his digits brushing against the sore walls of his soaked passage. Derek not only fucked him hard, but repeatedly until the sun began to rise only a minutes ago.

 

The teen came untouched at the thought, ropes of white splashing onto his belly and chest. The fist in his mouth prevented him from making a sound, and it was a good thing too. Because then he was able to hear the sound of a car—the rev of a certain Camaro—speed off into the distance.

 

Stiles grinned. He decided that he quite liked Derek’s visits.

 

TBC…

 

**Notes for the Chapter:**

> Comments are crack, so gimme a fix! :-D


	3. And When the Princess is Awake: Derek’s Return

Stiles barely manages to prevent himself from tumbling to the floor after one of Derek’s particularly hard thrusts. They started off in the middle of the bed, but their furious fucking actually propelled him across the soft, plushy surface to the edge. Now Stiles’ hanging off the side of his bed with his hands pressed flat against the wooden floor below him and his ass raised high in the air. Derek is kneeling behind him, pounding his hole relentlessly, the Alpha’s fingers bruising the pale skin of his hips.

 

“Tell me how good this feels,” Derek growls out.

 

Stiles moans loudly while Derek’s cock slips in an out of his hole at a punishing pace. “So fucking good. I love when you fuck me hard. I love when you make me your bitch,” he hiccups. And he does: he really means every single word. Stiles loves how rough the Alpha is with him—how dominated he feels.

 

“I know you do. Your hole is such as slut for my cock, pulling me deeper inside you. Feel so hot and tight around my cock. Your hole was meant for fucking an Alpha.” Derek reaches down to slip his fingers through Stiles’ hair, grabbing it and yanking him back up so he could bite the soft flesh of his neck—so he could mark him. “I can’t wait to cum and fill you up nice and full. To see your belly full of my cum.”

 

Stiles keens and nods frantically. He wants that too. He wants it so badly.

 

Just then the front door downstairs opens and shuts, and his father calls out to him. “Stiles, I’m home. Come down for lunch in 5. I brought home take out.”

 

Stiles panics. On one hand he doesn’t want to stop at all. He just wants to ignore the entire goddamn world so he can continue to get pounded like the slut he is. But on the other hand, Stiles knows his father well, and he knows that if he doesn’t make an appearance downstairs soon, his dad will come _upstairs_ to get him. And his father finding him with Derek balls deep inside of him is just not on his list of things he wants to have happen…ever.

 

Derek maneuvers the teen to his bedroom door, all the while with his cock still deep inside of him and moving though at a slower pace. The only sound is the jingling of Derek’s belt. Because oh yeah, he forgets to mention that throughout their entire “fucking” session he was completely naked while the Alpha was completely clothed save for his jeans which was unfastened yet still seated on his hips.

 

Derek opens the door. “Say something.”

 

Small tears form in the corners of Stiles eyes as Derek hits his prostate dead on. “Huh?” he breathes out deliriously.

 

“Say something or he’ll come up here.”

 

Footsteps sound, stopping near the foot of the stairs. “Stiles did you hear me?”

 

He tries to keep his voice even and normal as he replies; “Y-yeah dad. I’ll come in five minutes.”

 

His father grunts out an okay while Derek chuckles in his ear. “I think I can make you _cum_ in four.”

 

He opens the door and gently pushes Stiles all the way out, leading him to the top of the stairs despite the teen’s protest.

 

“What are you doing? My dad might hear us and come to investigate. I don’t want him to see us.”

 

Derek lies down onto the floor and pulls Stiles onto his lap so the teen’s back presses against his chest. “Then don’t let him hear us. Stay quiet and we’ll be fine.”

 

Stiles tries to protest but his mind goes completely blank when the Alpha slips inside him again. He lets Derek manhandle him however he wants, the older man eventually settling for holding Stiles legs up and open while he pumps his thick cock up into his hole. It feels so good to be open like this and Stiles is sure he looks like a wanton whore, getting fucked literally a few feet away from where his father is. He wants to cry out so badly at the thrill of this—of the thrill that he could be caught in this compromising position at any moment. And for a split second he doesn’t care if he does get caught—he doesn’t get care if his daddy catches him with his legs wide open and a thick cock furiously pounding his hole while he bounces up and down on Derek’s lap.

 

His father then calls out from the kitchen. “Stiles, are you coming?”

 

Yes, he thinks. Cause the mere thought of someone possibly watching him getting fucked out his brains is enough to send Stiles over the edge and with a muffled cry—because Derek is smart enough to slap a hand over his mouth—he comes all over his chest and belly. He trembles above Derek, his hole contracting and spasming around the hard length in his passage. His breathing is rapid and he can literally hear his heart pounding in his ears…

 

And he can also hear heavy footfalls coming closer to the stairs. It’s a good thing that he’s not near the edge where someone could see him if they were standing at the base. Especially because Derek hasn’t come yet, his hard cock still thrusting a mile a minute.

 

“Stiles?” The first stair creaks under his father’s weight as he slowly ascends.

 

Stiles whimpers as Derek fucks him even faster, and Stiles is grateful that the Alpha wasn’t completely naked because the sound of Derek’s balls slapping against his skin would have been unmistakable, even to his father’s ears.

 

The second stair creaks.

 

“Derek,” he whimpers partly out of need because he is already half hard again, but mostly out of panic. Now he isn’t so sure if he wants daddy dearest to find him riding Derek in their hall way.

 

“This is fun, isn’t it Stiles,” the Alpha chuckles quietly.

 

The third stair creaks.

 

“Times up Stiles,” the older Stilinski calls out.

 

Stiles almost laughs at his father’s choice of wording. “Yeah Derek, times up,” he whispers back to his Alpha.

 

Derek growls and changes his angle in response, targeting the teen’s sweet spot in revenge. Stiles suddenly forgets that his father is mere seconds away from seeing him and he cries out before Derek can stop him. Luckily for Stiles, the cock inside him belongs to a werewolf with super abilities, because even though his dad quickens his ascent up the stairs, Derek already has them both off the floor and into his bedroom before the Sheriff makes it to the top.

 

“I’m fine dad. Go back downstairs. I’ll be right behind you,” Stiles yells shakily.

 

He presses his cheek against his bedroom door as Derek once again resumes fucking him. They both hear his father take a few steps towards his room before he mutters something about weird teenagers and goes downstairs again. “Well lunch is ready if you want it,” his dad yells out.

 

Stiles releases a deep breath just as Derek seizes up behind him. He shutters as the Alpha’s liquid heat soaks his passage, filling him with so much cum that it seeps out and runs down the backs of his thighs.

 

He waits until Derek eventually pulls out before he turns around in his arms and swats him upside the head. “I hate you,” he says while trying to really mean it.

 

Derek looks down between them to Stiles’ cock which is fully hard again and straining alongside his cum-slick belly. “No you don’t.”

 

They stare at each other for a few moments before they break out into laughter—the kind that looks good on Derek as it softens his face and the steel edge of his jaw. Delighted that Stiles could do that to him, he reels Derek in for a kiss. “No I really don’t,” he says against his Alpha’s lips. “Feel free to fuck me like that anytime.”

 

Derek moans, kissing Stiles hard and deep before he pulls away. He wraps a hand around Stiles’ cock, stroking it leisurely while he looks into the teen’s brown eyes.

 

“Glad you approve. Because I’ll be fucking you all over every inch of this house.”

 

Stiles whimpers, thrusting into Derek’s hand with a huge grin on his face. He can’t deny that calling Derek over to his house today was the best decision he’s made in his life to date, and the prospect of more sex to come had him teetering over the edge once more. “Yes Alpha.”

**TBC…**


	4. Best Friends 4 Life

Scott was undoubtedly the pig of the lot. Stiles and Scott hung out all the time, so Stiles should have been aware that his best friend’s sloppy habits wouldn’t have changed just because they started fucking. Every day after Scott came over, Stiles had to pick up crumbs of food from his bed and pillows, and one time there was even a whole slice of pizza wrapped up in between the sheets. It was gross, and Stiles started to wonder if maybe he should ban Scott from his bedroom altogether.

 

It didn’t really help to improve his idea of his best friend when he noticed how sticky and dirty he was in the mornings, often covered in his own cum and whatever food Scott had eaten in his bed the night prior. I mean, what did Scott think this was? A slumber party?

 

But as he cleaned up around his room completely naked, something clicked inside of Stiles’ brain and he smiled. Yeah, Scott did think it was a slumber party. And he knew why. Years ago when they were both thirteen, Scott had stayed at Stiles house because at the time, the werewolf’s parents were going through a messy divorce. Their parents had let them stay home from school and they had played video games all day long and had rocky road ice cream, Cheetos and purple Skittles for lunch. At night, after Stiles’ dad had let them play in the cruiser (with the ignition turned off because the Sheriff knew the crazy tendencies his son had on occasion), the boys had laid down in their makeshift tents in Stiles’ room. They were on their backs and side by side, so close that they were touching. “I wish this would last forever,” said Scott.

 

Stiles shifted his right arm, grimacing as he peeled flattened, warm Skittles off his arm. He flicked one at Scott. “I wish you would learn to clean up after yourself.”

 

The werewolf smiled sheepishly, curling into Stiles and placing a hand on his belly. “Sorry Stiles. But I really do mean it. I wish this could last forever.”

 

“What? Skipping school, playing games and eating junk food all day? Sorry buddy but you’re all alone with that one. I have to keep this good looking figure somehow.”

 

“No, not that. This.” He hugged Stiles. “I want this to last forever. I want us to last. Promise me that we’ll stay best friends forever.”

 

Stiles turned over onto his side to face his best friend. “Of course Scott. No matter what, nothing will tear us apart. We won’t be like them,” he whispered, knowing that Scott would understand the reference to his parents and their divorce. He held out his hand, and when Scott did the same he linked their fingers together.

 

“Stiles, can I tell you something without you getting mad at me or thinking I’m weird?”

 

The younger Stilinski nodded. Scott took a deep breath and looked away to collect his bravery. When he gazed at his friend again, he breathed out “I love you.”

 

There was a moment of silence before Stiles laughed, the small dark freckles on his cheeks bouncing with every giggle. “That’s it? That’s all that was? You should have seen how scared you looked man. I thought you were going to die or something.”

 

Scott frowned and tried to pull away but Stiles wouldn’t let him. Instead he pulled his friend even closer. “I love you too Scott. I don’t think that’s weird to say. I’ll always love you.”

 

Scott beamed at Stiles and before the paler boy could blink, he surged forward and pressed his lips to his own. It was an awkward kiss full of bad technique and dry chapped lips on both parts. But it was comforting nonetheless and full of warmth. And both boys found that they liked kissing each other. They got better at it as they continued to kiss under the cover of darkness, and when the Sheriff found them in the morning, they were wrapped in each other’s arms with their noses pressed together and slight smiles on their faces.

 

Stiles walked over to his dresser where a picture of himself and his best friend was taped to a corner of the glass. He never thought that years later after they shared their whispered confessions of childhood love that they would indeed become lovers. He wondered what Scott was like in bed and how the young werewolf chose to fuck him when he was sleeping. And a part of him is amazed that he could sleep through their fun times as well. He’s seen Scott naked before. He knows he’s a _big boy_. In fact, Stiles wasn’t sure if Scott’s dick actually qualified to be a dick seeing as how it resembles more of a third leg. His nickname in his head for his best friend has always been tripod.

 

He began to wonder what their nightly ritual was. Did Scott hold him close as he had that night all those years ago? Did he murmur soft words of love as he slipped his giant cock inside Stiles tight hole? Did he run his finger through Stiles’ hair and kiss every mole on his body as his cock fucked itself deeper and deeper into the pale body beneath him?

 

Stiles moaned loudly. He slammed the picture in his hands onto the dresser, and gripped the grooved edge tightly, his nails digging into Cherry wood. He didn’t realize that amidst his pleasurable reminiscing, he had three fingers plunging in and out of his still slick hole at a furious pace. He imagined that it was Scott fucking him so hard and so deep, pounding his prostate dead on. Stiles spread his feet further and bended over, curling his fingers to get them in as deep as they could get. He mewled in delight when he was able to wriggle his pinky finger in alongside the other digits, the stretch so sensational that it tipped him over the edge. He cried out as he came, streams of white literally painting the photograph in its entirety.

 

 

**TBC...**


	5. Nothing Cums Between Friends

It was late at night the following week when Scott tried to sneak quietly into Stiles room with a box of pizza. His usual clumsiness was replaced by an impressive skill of stealth. But it was all for naught when he noticed that Stiles was awake and sitting up in bed in his pj’s rather than fast asleep. And when he noticed that he bumped into a small table that was near the window, the small stack of books placed on it colliding to the floor with a loud thud. After the initial embarrassment died down and the flaming heat that burned Scott’s cheeks began to cool, he waved sheepishly at Stiles.

 

“Hey.”

 

Stiles smiled warmly and waved back. “Hey.” When the teen didn’t move Stiles rolled his eyes and patted the space on the bed next to him. “Well what are you waiting for? A written invitation?” There was no bite to his words.

 

Scott laughed and went over, toeing off his shoes and tossing his jacket to the floor. The pizza ended up on the table next to the bed. He sat next to Stiles, back against the headboard but still at an arm’s length apart. “I didn’t think you’d be awake,” he said lamely.

 

Stiles arched an eyebrow. “Prefer to molest me in my sleep, do you? Well if you get me some Benadryl then we can make that happen.”

 

They both chuckled at that, and when the laughter ceased moments later, Scott nervously began to speak. “It’s just easier to be with you when you’re asleep. Less likely to be judged and all of that,” he said as he scratched the side of his neck.

 

Stiles frowned. “Judged? Why would I judge you Scott? In what way?”

 

“Because I’m not the only one that you’ve been with,” came the deadpanned response. “I can smell them on you when you’re close. Sometimes I can still smell traces of them…you know…down there.”

 

Stiles blushed and nodded understandingly. “Makes sense,” he said. Slowly he crawled forward until his face was mere inches away from his friend’s. “Would it make you feel any better if I told you that you were my first?”

 

Scott snorted. “I kind of **know** that I wasn’t Stiles.” Nonetheless he pulled the paler teen close enough that he was half-way straddling his waist. “So how does that work?”

 

Stiles grinned as he ran his nose all the way up from the base of Scott’s neck to the soft spot behind his left ear. “You were the first person that I let into my heart. All those years ago when you held me close and kissed me for the first time. Do you remember?”

 

Scott smiled and leaned into Stiles’ touch. “Yeah. We were kids though.”

 

“True. But the words spoken are still true. I love you Scott. My first love,” he whispered as he pressed his lips to his best friend’s. _My only love_. That was the part that remained unspoken—the part that would never be spoken. Stiles had way too much love and affection in his heart to give to be tied down to one person. That’s just the way things were and Scott would have to accept them at some point.

 

But maybe not today.

 

“Still wish I was your first,” Scott grumbled.

 

Then something changed. The atmosphere changed. Stiles tensed in his arms and whimpered slightly. “I don’t know if I’m ready Scott,” he said timidly. Instantly the werewolf became confused. “Ready for what?”

 

Stiles swatted at his chest at the absurdity of the question. “For tonight dummy. I’ve…I’ve never been with anyone before and I’m nervous. What if I don’t, you know…do it right?”

 

“Stiles what are you talking about,” Scott began but when he saw the glint of amusement and a hidden challenge in Stiles eyes, the werewolf immediately realized what was going on. _He wants to play a game._

 

So Scott went with it.

 

“Don’t worry baby. I’ll teach you.” The baritone of Scott’s voice sent shivers down Stiles’ spine. He ran his hands up and down his sides, his tanned hands squeezing paler hips. Stiles whimpered and pressed even closer to the wolf, gasping slightly when his inner thigh brushed against the hard length between Scott’s legs. Naturally his curiosity got the best of him and soon Stiles’ fingers were trailing down Scott’s chest and stomach until they came to rest on the imposing bulge. “It’s gonna hurt,” said Stiles wide-eyed.

 

Scott chuckled. “Only for a little bit. Then it’s gonna feel really good. I promise you.”

 

“Do you mean that? Will you make me feel good?” Boy Stiles was putting on a real show. His eyes were wide and watery as if he were a terrified virgin. It made Scott and his wolf very happy.

 

“Yeah baby I will.”

 

“Then show me Scott. Show me how you’ll make me feel good. Touch me. Fill me up. Make me scream.”

 

Those were words to live by. In mere minutes Scott had divested himself and Stiles of their clothes and had three fingers stretching Stiles in preparation for his cock. The pale teen moaned with every thrust of the thick digits. He whimpered and clenched at the wolf’s fingers whenever they seemed to slip away only to sigh when they went back in. It was heaven to feel Scott within him, but hell when he pulled out completely and replaced his hand with his member.

 

Scott pushed in slowly, the head of his thick cock pushing past the loosened ring of muscle after a few tries. It felt like Utopia to Stiles and he wanted nothing more than to yell at his friend for him to push it in all the way and fuck him hard and fast, but he had to play the part. A virgin would never say something like that.

 

He _had_ to play the part. For Scott.

 

“T-take it out. ‘Ss too big. Take it out please.” There was a desperation to Stiles voice that made Scott think for a split second that he might be telling the truth. But the thought that Stiles had never had a cock in him as big—the possible idea that Scott could have trumped the other members of his pack in such an intimate way, had his wolf thrumming in pleasure. “Can’t baby,” he said as he kissed the corner of Stiles’ mouth.

 

“No please. Take it out Scott. You’re too big—your cock is so huge. My hole’s too small. You’ll never fit.”

 

Scott chuckled against his lips, the small puffs of air making the corners of Stiles’ mouth curl upwards into a smile. “Just watch me,” he whispered back, pushing further and further into Stiles until he bottomed out completely. He captured the pale teen’s lips, swallowing the cries as he pumped languidly into the molten heat surrounding his cock.

 

They rocked together passionately, but unhurried. Savoring the time that they had to explore each of their bodies. With every thrust Scott whispered words of affections. _Perfect. Perfect._ That became the mantra spoken by the two of them. Stiles reached up to smooth back Scott’s hair from his face, making sure that the wolf could see the love and satiation in his eyes. He wanted Scott to see his face when he came, painting their bellies with streams of white. For Scott to know that his cock alone brought him to the point of pure ecstasy. And he wanted to have a clear view of Scott when the wolf came moments later, filling his passage with liquid fire, searing him the best way.

 

“I love you Scott,” he panted when his friend pulled out and fell onto the bed beside him.

 

The wolf blushed and pulled Stiles close, their chests flush against each other. He nipped at Stiles’ nose and pecked him quickly on the lips. “I love you too Stiles. And thank you for…everything,” he said sheepishly.

 

Stiles winked at him before closing his eyes. “That's what best friends are for,” he whispered before the realm of sleep overtook him and he succumbed to the darkness.

 

**TBC...**


	6. Roses are Red, Violets are Not...

**Notes for the Chapter:**

> Hey all! Sorry I've been away for so damn long. Working on bettering my life and career. But I'm back now and I promise that I will finish this daggone fic! 
> 
> Anyways, I hope these new chappies makes up for my absence. Ladies and Gentlemen, I present to you...some Stackson lovin!
> 
> Also, I realize that Jackson is hella OCC in this chappie. Roll with it, lol! :D
> 
> Enjoy! :)
> 
> -CM

**6**

 

Stiles was utterly shocked when Jackson visited. He would have thought that after years of the jock’s torments, both with his possession of the only girl he’d ever loved, Lydia, and his place as the head of both the swimming and lacrosse teams, that the newly turned werewolf would have wanted to assert his dominance over him. You know, a little bruise here, a little patch of missing skin and hair there. But Jackson didn’t. It made Stiles think at first that perhaps Jackson never came to him and that it was someone else. But every wolf that he’d been with so far had left evidences of their time with Stiles in some way, shape or form. Derek left him sore, Peter left behind clothing, Scott usually tore apart his sheets, and Isaac left behind written messages and lipstick kisses all over his body. Jackson ended up being no exception, but what surprised Stiles the most, is what the lacrosse player decided to do. One morning Stiles had awoken to find three dozen bouquets of red, white and pink roses, accompanied by a box of candy and a letter. Stiles thought he was dreaming as he crossed the room, the sweet aroma of the roses caressing his nose as he took a whiff. He lifted the card, briefly inspecting the expensive Italian stationary before reading the text within.

 

_You know who I am—who left all of these things for you. You must be surprised that I came to see you, and that I left you all of these things. To tell you the truth Stiles, I’ve had thoughts about you before. About being with you ever since you made first line on the team and I saw you play. I always wondered what it would be like with you—to have those long legs wrapped around my thighs. When I came in through your window last night, I could feel my heart beating loudly in my chest. I was so nervous. Strange huh? That someone usually as confident as myself is admitting that I got nervous—that I got weak. Well, you do that to me Stiles. You make me weak._

 

_I thought it would have bothered me that the others in the pack have had you—that they’ve claimed you in some way. But when i saw you last night, in only a pair of checkered boxers, I knew that my time with you would be just as special. And that I would claim a part of you too, in my own way._

 

_I wish you could have seen yourself, the way your legs looked around my waist as I slowly pushed inside. You moaned and whimpered in your sleep, pulling me deeper inside of you until I bottomed out. I remember looking down at your face—a perfect picture of innocence—when I started to move. Did anyone ever tell you how gorgeous your freckles are? How badly I wished I could kiss and lick every single one that covered your body? Of course being the coward that I am, I never said a word. But just know that I would. In a heartbeat, if you asked anything of me, I would do it for you._

 

_I tried to stay inside of you for as long as I could; fuck you slow and deep. Your hole fit around my dick like a sleeve, clinging to me when I thrust outwards, as if you were afraid I’d leave you. But it was so hard… **so** hard not to pound you into the mattress, to hear you whine and moan just a little bit louder in your sleep. And I would have done too—brutally pound your sweet hole—just to see if you would wake up and cum from my cock. _

 

_I remember looking down at us, bending you nearly in half so I could watch myself slip in and out of you. You made this adorable sound in your sleep, when I thrust inside of you, seeing if I could get any deeper than I already was. It was such an enchanting sound—a cross between a whimper and a moan. It made me impossibly harder when I heard it, so I tried to make you make that sound again. It took a few tries, but when I did it, I realized immediately that I was hitting your spot. So I did it again, and again, and you cried out perfectly each and every time. I wonder if your dad heard you moaning like that. He was home and in his bedroom as I fucked you._

 

_You’re probably wondering where all of this is coming from—the tokens of appreciation, this letter…etc. I’m not the jerk you think I am, even though you have every right not to believe that. It’s not like I’ve done a good job at convincing you otherwise throughout the years. I only wished that we could have looked into each other’s eyes when I came inside of you. Because maybe, just maybe, you would have seen the sincerity I hold within._

 

To say Stiles was stunned as he read the letter was the understatement of the year. He never knew that Jackson could be so….deep with his words. He never knew that he could be so utterly romantic. That he could be nice. And Stiles most certainly didn’t know that Jackson had ever desired him in a sexual way. The guy didn’t necessarily show it. Stiles wasn’t sure if he preferred this side of Jackson or the one he’s known for so long.

 

_I’m coming over tonight Stiles, and I’m going to fuck you again. I doubt I can stay away from your hole for too long. Stay awake for me tonight Stiles. I want you to feel me, to see me, to hear me whisper filthy things like how bad I want to fuck you in the middle of the locker room while our teammates come back from practice. Damn, I’m hard right now just thinking of being inside you, pumping you so full of my cum until it drips out of you and onto your sheets. But for tonight, I have a special request…._

 

**TBC....**


	7. Lydia watching us fuck is kinda really hot.

**Notes for the Chapter:**

> Smut is so hard (hehe) to write, but I hope I'm doing a good job. 
> 
> Also, new tags (Slut shaming, Pack Whore, Slight Feminization) were added specfically for this chapter, as well as for Peter's chapters. Please be advised if these new tags are ones that you are not comfortable with. Thank you.
> 
> -CM

**7**

 

Stiles moaned as Jackson fucked him on his bed. They were lying down on their sides, Stiles’ back pressed firmly against Jackson’s chest. The jock was holding his right leg up, thrusting slowly in and out and nibbling on his ear at the same time. "So fucking tight, baby." Stiles felt like he was fucking floating on air every time Jackson brushed against his prostate.

“Harder.”

The word was spoken so soft, so seemingly innocent, that Stiles wasn’t even sure that he heard it in the first place. Because he wasn’t the one that said it. No, the order came from the petite redhead that sat in the corner watching them.

Stiles moaned even louder when the thrusts became harder, each one making the bed vibrate just a little more. His eyes fluttered close at the delicious pleasure, his legs trying to close on instinct to pull Jackson’s fat cock deeper inside him.

“Keep the little slut’s legs open.” Jackson obeyed, prying Stiles legs open so that Lydia could see them fucking. “Fuck him faster.”

She sat there almost statuesque, her face expressionless. Dress from head to toe in Gucci, she didn’t touch herself. She didn’t participate in any way except to voice the occasional command. She was so mesmerizing and intimidating that Stiles found himself torn between staring at her and looking away. He should be ashamed of himself—he was technically fucking her boyfriend right in front of her. But this is what she wanted. She wanted to watch Jackson fuck him—to see what her boyfriend was running off in the middle of the night for. When he read Jackson’s letter, he found himself so hard at the thought that Lydia would see him like that. The girl that he loved for most of his life wanted to see him fuck her boyfriend. It was so unbelievable that Stiles nearly dismissed the letter as a joke. But when they showed up as promised, Stiles knew otherwise. And that’s how they ended up here now.

Slowly Lydia rose from her chair and made her way to the bed, toeing off her shoes and crawling towards them. “Does his cock feel good inside of you?” When Stiles didn’t respond fast enough, she slapped him. His cock leaked a little more. “Answer me Stiles!”

“Yes,” he croaked, voice cracking as Jackson pounded his prostate dead on. “Yes it feels good.”

“What feels good? Say it,” she growled.

“Your boyfriend’s cock,” he panted. “It feels so good inside my hole, fucking me deep.”

Lydia sneered in disgust. “You’re such a slut Stiles. You don’t have any shame, do you? Tell me what you are.”

“I’m a whore—a cock hungry slut.”

Lydia chuckled darkly. “I bet you wish you had a pussy, don’t you Stiles? Is that what you think your hole is? Some sort of wet cunt? Pull out Jackson.” Like a servant, he followed her order, his cock rock hard and flushed red. Red painted fingernails grazed the rim of Stiles' hole, her thumbs stretching it wide enough for her to lodge a wad of spit directly inside. Stiles’ moaned at the degrading act—at the sight of Lydia between his legs inspecting his hole like she had every right to do so.

“Control him Jackson, make him beg,” she said sternly. Instantly one of Jackson’s hands curled in Stiles’ hair, yanking it back. “Beg for my cock you whore,” Jackson growled in his ear.

“Please,” Stiles moaned weakly. “Please put your cock in me. Please fill me up. My hole feels so empty.” Stiles earned a slap for that and he nearly came from the sting of it. “Not your hole Stiles. What’s it called?”

“M-my cunt. Fuck my cunt Jackson.” Like that Jackson thrust in with one rough stroke, his pace immediately fast and brutal. Stiles’ eyes rolled in the back of his head, his toes curling taut.

“Oh god your cock feels so good Jackson. Stretching me so wide. Fuck yes.”

“Maybe you should cum in his cunt. Breed him like the little bitch he is,” said Lydia. Casually she ran a red painted nail up the length of Stiles’ cock. “Isn’t that what you want slut? You want Jackson’s cum inside of you?”

“Yes,” he whined. He was so close to coming himself that if the wind suddenly blew, that would be enough to set him off.

“Punish him,” she said to Jackson with a flick of her hair. She reclined next to them on the bed, watching with relaxed interest as Jackson flipped Stiles onto his belly, grabbed his hips, and fucked him furiously from behind. Stiles mewled as he was fucked so hard that the feeling bordered in between pleasure and pain. The headboard slammed against the wall so loudly, and with a fleeting thought the teen was grateful that his dad decided to take the overnight shift at the station. What would his father think if he knew that his son liked getting bred by werewolf cocks—that there was a different man fucking his son nearly every night in his room that was only five feet away?

“I want to hear you beg me for Jackson’s cum you nasty slut. Beg me for permission.”

Stiles’ eyes were filled will delirious tears when Jackson yanked his head by his hair because the redhead commanded it. The whole situation was so fucking hot, that Stiles almost wished that the entire pack was here to witness him getting fucked like this.

“P-please…please Lydia. Please let me have Jackson’s cum. I need it so bad. I need him to fill me up, stuff my cunt so full of cum…make me wet with it,” he pleaded.

Lydia waved a hand. “Go ahead Jackson and make it quick,” she drawled with a bored expression, as if she wasn’t lying next to her boyfriend fucking the stuffing out of her friend. As if Stiles wasn’t getting his hole brutally fucked like a two-bit prostitute. She even pulled out her phone, making a sideways comment that she was on Twitter. That, plus the feeling of Jackson emptying his load inside of him, scalding him with his hot cum, was enough to push Stiles over the edge. With a cry he came so hard, ropes of white spurting all over his sheets below and even hitting him on his chest and chin.

When Jackson pulled out a minute later, globs of his cum followed making Stiles shiver and whimper at the feeling. He was still seeing stars when Lydia grabbed his chin, forcing him to look at her. “I’m glad that you had fun Stiles, but don’t get any silly ideas. Jackson is still mine—you’re just a hole that he gets to fuck on occasion because I _allow_ it. I hope this is all perfectly clear,” she said darkly. When the teen nodded, her expression changed to a pleased one, and she leaned forward to place a soft kiss on Stiles’ lips, her tongue swiping up a bit of his own cum from them. She made sure that he watched as she rolled Stiles' cum around her tongue, spreading it across her lips like it was a new lip gloss. “Good boy,” she said with a wink. She fell back against the pillows with a small smile. “Now lick Jackson’s cock clean so he and I can go home. We have a Biology exam in the morning.”

“Yes Lydia,” he said, smiling when Jackson’s cum-covered cock came into view.  Stiles looked up hazily to see Jackson smile and wink at him, his whole body feeling extra tingly when the jock caressed his cheek and pulled him closer by the gentle grip he had on his neck. He giggled and winked back. Did Stiles ever mention how much he loved being the pack whore?

 

**TBC….**

**Notes for the Chapter:**

> How was it? Too porny? Not enough? Let me know! :)
> 
> Next Up: Peter


	8. Its just a wolf, Little Red.

**Notes for the Chapter:**

> Hey everybody!!! Sorry it took a while to update. Just when I thought I would have more time to write my fanfics, my acting career just took off! Like a rocketship! (Starships are meant to fly :D) But I am going to try to finish all of my WIP's, don't worry. 
> 
> But as a major note, even though I labelled this as a "Five times" story, and intended to include my Stiles/Isaac chapters, its not looking likely anymore. I just can't seem to get anything down on paper for those two, sorry. I struggled for a while, but just...nothing. Sorry folks. I DO however, have an epilogue planned, but it might not be everyone's cup of tea, so it will be OPTIONAL. I will include that in the taglines so that people don't take my head off, lol.
> 
> -CM

**8**

 

It would be a lie if Stiles said that he was a bit cautious letting Peter fuck him. Let’s face it, the older werewolf was a teensy bit bat shit crazy, and he had no problems relaying that over and over again to the pale teen and anyone else that he came into contact with. But while a huge part of Peter scared the hell out of Stiles, the remaining bit fascinated him. And for good reason. The sex was rather amazing and athletic if the bruises and aches in Stiles' neck and back when he awoke were any indication. But let’s just say that this particular wolf had a few interesting….quirks that Stiles rather liked. Plus the pretty gifts that Peter left him were fun as well. Of course he was asleep when he received them, but his imagination on what Peter did with those things was thrilling enough.

 

Like the purple panties that he bought Stiles a few weeks ago with the frilly black, lace edges. Those were nice in their design, and they hugged him in all the right areas, nestling his cock and balls in a cradle of warm silk. But as sexy as they were, what really got Stiles in gear was the fact that Peter took the time to shave his legs, not that there was much hair there to begin with. But no, his legs were in fact silky smooth to the touch when he ran his fingers down the length of his calves. and in the glint of his bedroom light, the teen noticed that his fingernails and toenails were painted in a shimmery shade of baby pink. Stiles shivered, a small wet patch forming on the front of his panties. No one had ever pampered him in that sense before, and he found himself craving that sort of attention again. But only this time, he wanted to be awake and alert when it happened, which he relayed to the nutty wolf when he saw him at the next pack meeting.

 

He half expected Peter to rebuff his idea outright, and possibly shame him for his desires in front of the entire pack. Because that’s the sort of thing that Peter does for shits and giggles. Instead, Stiles received a piercing stare that nearly stripped him bare and made his cock hard in 0.3 seconds. Peter had licked his lips, dragging his eyes over the entire length of Stiles’ body before nodding curtly and flashing a ravenous grin. _“Anything you want Princess,”_ he had whispered lowly into the teen’s ear, pinching his behind when the others weren’t looking.

 

And it was that interaction that led to the current events of Stiles’ day. He had just finished showering when he came out of the bathroom to find a medium sized gift bag lying on the middle of his bed. Stiles paused in the middle of towel drying his hair to inspect the contents, smiling when he saw what was inside. Beside the bag was a note, the handwriting unmistakable. The teen couldn’t help glancing around the room even though he knew the wolf responsible was long gone. He half hoped to see Peter leaning against the wall behind his bedroom door, but no such luck. So he read the letter, no less pleased by what was written.

 

        _Princess,_

_Put these on. Skip school today and make sure we have no interruptions._

_Don’t disappoint me. The consequences won’t be favorable if you do._

_And remember… you asked for this._

 

_-P.H._

 

Stiles peered down at the contents of the bag, his lips curling upwards into a smile. Yes he sure did.

 

**TBC…**


	9. Awww, is that for me Little Lamb?

**Notes for the Chapter:**

> Hope you enjoy this chappie! Please be aware that new tags were added based on the kinks addressed in this chapter. You were warned accordingly.
> 
> Also, Un-betaed. I will fix errors as I see them. Sorry about that.
> 
> Enjoy! :D
> 
> -CM

**9**

 

As quietly as it could be managed, the pale teen shut the front door and lightly crept up the stairs, making sure to dodge the ones that creaked. The house keys were clenched in a tight fist so as to make no noise. There was no telling whether dad was home, but no chances were being taken. If he was home while school was still in session, there sure would be hell to pay. Or a lengthy explanation would immediately be required. The teen didn’t find either of those situations necessary or appealing. Plus the main objective was clear: make it to the bedroom, hide out for the better part of the day, and make up a bullshit version of the events of the school day in case dad asked any questions later. Easy. No sweat. Totally doable.

Except a voice calling out as the teen passed by the door of the home office had her nearly collapsing of shock.

“Genna? Is that you? What are you doing home?”

Genna sighed, pushing the office door fully open to stand sheepishly in front of her father. Instantly her fingers played with the hems of her pleated plaid skirt, her bottom lip between her teeth.

“Dad! You scared me to death. I didn’t think you’d be home. Why aren’t you at work?”

Her father frowned, the paper that he was reading before she came in slipping from his grasp. “I’m confused as to why it should matter seeing as how you should still be in school. Which you aren’t,” he deadpanned. “Care to explain?”

“I left early.”

“Yes Genna. I can clearly see that,” he replied slowly. “The question is why?”

Genna looked down at the ground. “I wasn’t feeling well, so the school nurse let me go home.”

Instantly her dad’s heated frown melted into a look of concern. “No one called me though. The school should have called me. I would have come to pick you up sweetheart.”

Genna shook her head, ebony locks swishing against her shoulders as she did so. “I begged them not to call you. I didn’t want to bother you with…this.”

Her father stood up and came from behind his desk, his hand grasping hers gently. He pulled her more into the room where he could get a better look at her. “With what? What’s wrong sweetheart?”

Genna glanced at her dad, her wide brown eyes capturing his before looking away once more. “It’s personal dad.”

He wasn’t buying that. “Genna darling; you’re all I have. If there’s something wrong then you need to let me know so that I can take care of you, just like I always do. Don’t I always take care of my little girl?”

“Yes daddy,” came the timid response.

Her dad smiled and pulled her closer, rubbing his hands up and down her arms. “That’s right. Now tell me what’s wrong. I know that I can be a bit of an old fuddy-duddy, but I promise I’ll do my best to understand. So what’s up?”

Genna bit her lip again, unsure of whether or not she should reveal the truth to her dad. It wasn’t like she wanted to lie to him. It was just that the truth behind her silence was a bit awkward in her mind. What if her dad laughed at her when she told him, or even worse, scowled at her and called her an embarrassment or something. She doubted he would do that, but still.

In her silence, her dad tried to take a stab at what was wrong. “Is…is this about your monthly friend? Do you need women’s things from the store?”

Genna’s head snapped up so quickly it almost snapped right off. “What? No dad, I’m alright with that stuff. It’s just that…well…something’s off with me and I don’t know what to do.”

“Off? Are you sick? Let me grab a thermometer so we can take your temperature.” When he moved to stand, Genna quickly pushed him back against the edge of his desk. “No dad, I’m not sick. Well not really—not in that way at least.”

“Okay,” he said slowly. “So what’s going on? The suspense is killing me.”

 _Deep breaths_ , she thought. _Might as well get it out. Things might get a bit awkward afterwards, but he’s your dad. He won’t disown you, silly._

“Well dad, I’ve been feeling a little odd…down there,” she whispered the last bit.

Peter frowned for a second in thought, before realizing what she meant. Oh, down **there** _._ He gave a tentative smile, trying his best to make his baby girl feel as comfortable as possible. “In what way Genna?”

“Umm,” she found it impossible to maintain eye contact as she said the next part, “I’ve been feeling a bit empty.”

Peter repeated the words, dumbfounded.

Genna nodded, shifting from foot to foot, stubbing the toe of her Mary Jane’s into the carpet. “Uh-huh. It aches sometimes daddy. And I didn’t know what to do. My stomach gets all fluttery, and my cheeks feel hot and I get that….ache down there. It gets unbearable daddy, especially at night.”

Peter licked his lips. Well he certainly wasn’t prepared for this. He had to clear his throat a few times to make sure that his voice was still functioning. “And what do you do when you get that ache down there sweetheart?”

Genna swallowed loudly, rubbing her thighs together subconsciously. That didn’t go unnoticed by Peter. “Itouchmyselfdaddy.”

Peter blinked. “What was that, love?”

“I said, I touch myself daddy,” she repeated.

He blinked again. “And does that help when you touch yourself?”

Genna nodded. “It does. Well it usually does. But it didn’t work today for some reason.”

Peter’s eyebrows nearly climbed off his face. “Today? At school?”

“Yeah. I got the ache during our sex ed lesson and couldn’t concentrate on what the teacher was saying, so I excused myself from class so I could go to the bathroom. I tried for so long to make the ache go away daddy. I used two fingers and everything. But it didn’t work.”

“T-two fingers?”

“Uh-huh, these two,” she said, holding up her index and middle fingers of her right hand. “I usually feel a lot better when I put my fingers inside myself, but today it didn’t work. I tried it in so many ways daddy: I tried it hard and deep at first, then slow and gentle, then quick and rough. And I made sure that I was wet enough and everything, but nothing worked. I think something’s wrong with me daddy.”

Peter felt himself drift off into a daze as his daughter spoke. He knew it was wrong to imagine his daughter in that situation, but he couldn’t help it. His cock swelled at the thought of his daughter finger fucking her needy little twat in a stall of the girl’s bathroom, moaning impatiently when her tiny fingers weren’t getting the job done. And standing in front of him in her white button down shirt, short skirt, and thigh high white stockings weren’t helping his raging hard-on. But fuck it, he already knew he was going to hell. Might as well enjoy every delicious sin he could get his hands on in the meantime.

“Is it still aching, baby?”

“Yes daddy. Worse than ever. That’s why I begged to come home. I was hoping to try again with my fingers before you got home. I was going to try three fingers this time,” she said excitedly. Peter groaned, her words going straight to his leaking cock. He made a vow right then and there that he was going to go against the law, and everything that was right and just.

“Okay baby. Well I’m glad I stayed home today and that you decided to tell me, because I can help you Genna. What you’re feeling is completely natural. Most women go through it—a little bout of female hysteria when they desperately need to be satisfied in order to think straight. So I’m going to help you get rid of that pesky ache once and for all. But I need you to show daddy where it hurts so that I can make it go away. Okay?”

Genna nodded, hopping up on her dad’s desk when he told her too. With her permission, he pushed her skirt up and slowly pulled her pink panties down, stopping at one point so that they dangled from one ankle. “Open your legs real wide and lean back so daddy can see everything baby.” Obediently she did as instructed and Peter groaned at the sight before him. “Oh yes baby, I see what you were talking about.” The puckered hole in front of him clenched constantly, winking enticingly at him. He longed to bury his tongue in that hole—make his daughter cum from nothing but that alone. But he had a different agenda in mind, so that would have to wait until next time.

“See daddy? This is what I do when it aches,” she said breathily, caressing her glistening hole with the pads of her two fingers. They sank into her quite easily only a moment later, languidly slipping in and out of her passage right before his greedy eyes.

“Fuck baby,” Peter hissed.

“But it’s not working daddy,” Genna panted. “It’s not working anymore. Not even when Jackson tried earlier.”

That caught Peter’s attention. “Who is Jackson?” he growled.

Genna’s fingers faltered in their rhythm. “Just a boy at school daddy. A friend of mine. I told him what was wrong with me and he tried to help me. But it didn’t work either daddy. His fingers couldn’t help me either. Daddy please help me. Make the ache go away.”

Peter shushed her, moving her hands away. “You can’t send a boy to do a man’s job,” he grumbled. “But it doesn’t matter. I’m here now and I’m gonna make everything alright baby.” He quickly unzipped his jeans, freeing his hard length that was practically begging for a hole to fuck. He wanted things to go differently—he wanted to take his time with her, introduce her to all of the joys of foreplay. But the thought of another person touching her in an intimate way drove his wolf insane, the desperate need to fuck being the only relevant thought on his mind. He barely had enough sense to grab the packet of lube that he had in his desk drawer, slicking himself up before positioning at her entrance.

Genna saw what he was going to do and panted even harder, her thighs quivering beneath her father’s touch. “Will that make me feel better daddy? Are you going to heal me with your cock daddy?” The question was posed so innocently, so coyly, but Peter saw right through that. He saw the mirth twinkling in those baby brown eyes--knew that the boy underneath all the pretty clothes was toying with him-- so he upped the game a bit. The only thing that tipped “Genna” off was Peter’s trademark grin, but she had little time to compose herself before he plunged in, sinking into the hilt and starting a punishing pace.

“Oh daddy,” she screamed, gripping onto his shoulders as he nearly fucked her into the afterlife. “Daddy, your cock is so big. So fucking full. It feels so good inside me,” she gasped, damn near squeaking when his cock brushed against a sensitive part inside her. White stars burst behind her eyelids with every thrust, the sensation completely overwhelming. The only sounds in the room were Peter’s harsh grunts, Genna’s breathy moans, and the creaking of the desk that she was being fucked on that swayed violently. Pens, books, and her father’s pendulum soon clattered to the floor. Her shoes bobbed in the air from their place around her daddy’s waist, her painted fingernails threatening to claw their way through his cotton t-shirt. Every time she tried to suck in a breath of air, her daddy fucked it right out of her, keeping her constantly on the brink of euphoria. It was maddening and exquisite at the same time. Especially since her daddy kept grunting out harsh words in her ear. “This little cunt is mine. No one else is allowed to touch you, do you hear me? Only daddy’s cock is allowed to sooth your aches from now on. I’ll kill anyone else who tries to take what is mine. I’ll fucking kill them,” he growled.

Genna nodded enthusiastically, too caught up in the sensations to give a fuck about anything else. “Yes daddy. Only yours. I’m your little girl. I won’t let anyone else touch me. I belong to only you,” she moaned, eyes clenched tight at a particularly rough thrust. When her daddy sought out her lips she eagerly gave in, mewling and whimpering when their tongues collided. “Daddy’s gonna fill you up nice and full baby girl. Gonna give you my cum sweetheart, make that ache go away,” said Peter when they pulled apart.

“Yes daddy, fill me up. Give me all of it,” she moaned, literally having to scramble for purchase when Peter started fucking her even harder, the desk threatening to tip over. Two brutal thrusts later and Genna shuddered at the feeling of her father’s searing cum filling her to the brim. It was so intense that it tipped her over the edge, pleasure thoroughly consuming her as her own wetness covered her stomach and skirt.

Stiles was the first to speak. “Never thought in a million years that you’d be into roleplay.”  
 

Peter shrugged. “Every psychopath has their quirk.” He lazily thrust inside Stiles, somewhat pleased when the teen hissed and whined that he was still sensitive. “So _Genna_ , huh?”

Stiles feigned a glare. “Close enough to my real name. Don’t ask furball,” he said quickly when he noticed that the wolf was about to say something.

“Alright, alright. Keep your panties on, little lamb.”

Stiles raised an eyebrow. “Thought you liked them better when they were off?”

Minutes later Peter pulled out carefully, leaning his head on Stiles’ shoulder with a slightly animated laugh. “Well that certainly made my day. So glad I didn’t kill you years ago. I wish I could still offer you the bite. One day hopefully. Anywho, was that worth missing a day of school?”

Stiles rolled his eyes at the wolf’s casual yet insane chatter, chuckling along with him. “You’re such a fucking pervert Peter,” Stiles said after the laughter died down. “Aww, but you did so well Princess,” the wolf cooed, squeezing the teen’s thighs for emphasis.

Stiles pushed him back, moaning when the movement caused Peter’s cock to brush against his sensitive entrance. “Why thank you… _daddy_.” The teen grimaced at that. “God, I’m gonna have a huge complex now, seeing as how I actually have a living father. I won’t be able to look at him for at least a week.”

“Oh please Little Red. You’re going to have more than one complex from now on. That’s what happens when you decide to fuck a pack of wolves,” said Peter with a grin.

He might be crazy as fuck, but there was something about Peter that reeled Stiles in every time. Spreading his legs wide, he grabbed the wolf by his shirt and pulled him in for a brief kiss. “Well then Mr. Big Bad Wolf, let me show you what else I have in my picnic basket.”

 

**;-)**

 

**TBC…**

**Notes for the Chapter:**

> This was by far my favorite chapter to write, lol. Love crazy Pete. What did you think?  
> Comments are crack, so gimme a fix, lol! :P
> 
> -CM


	10. I'm Coming Home; Tell the World That I'm Coming Home

**Summary for the Chapter:**

> Final Chapter! Yay!!!

**Notes for the Chapter:**

> This chapter is OPTIONAL. It features Stiles' father, John Stilinski. Keeping up with the theme of this entire story, I think you can guess what happens. 
> 
> READ AT YOUR OWN RISK!

* * *

**Epilogue**

 

Sheriff Stilinski sat behind his desk at the station, his eyes glued to the screen of his laptop. He swiped a hand over his face, his mind racing. Officers had come into his office various times to ask him questions or show him their daily reports, but he couldn’t really pay them any attention, sending each of them on their way with a distracted hand wave or an unintelligent grunt. For the past couple of hours he could not nothing more than blink and breath heavy.

 

Security cameras.

 

He installed them all over his house when he noticed strange things happening around the place. He would hear weird sounds in the middle of the night when he’d return home from 15 hour long shifts. Moans that would immediately stop as soon as he’d drop his keys on the table by the door. The house constantly smelled thickly of sex, so much so that he nearly passes out on the doorstep every time he comes home. He didn’t think Stiles was sexually active, but it shouldn’t surprise him. Stiles might be awkward and lanky, but he was still is a teenage boy. Sex was probably engrained in him down to the cellular level.

 

But who was Stiles fucking?

 

The Sheriff came home for lunch one day to enjoy a meal with Stiles, and he swore on the drive home he had passed right by Derek’s black Camero parked a few blocks down. As far as he knew, Derek wasn’t familiar with anyone in the area. Parking the squad car away from the house, John stealthily snuck around the side of his house, standing underneath Stiles’ open bedroom window. The sounds of fucking was unmistakeable.

 

“Tell me how good this feels,” he heard Derek growl.

 

“So fucking good. I love when you fuck me hard. I love when you make me your bitch,” was the Stiles’ strained reply.

 

“I know you do. Your hole is such as slut for my cock, pulling me deeper inside you. Feel so hot and tight around my cock. Your hole was meant for fucking an Alpha. I can’t wait to cum and fill you up nice and full. To see your belly full of my cum.”

 

Well, holy shit.

 

So Stiles was the one getting fucked, and properly by the sound of it. It made John feel out of place and yet insanely curious. So he installed the security cameras around the house, including Stiles’ bedroom. He just had to see what was going on. He just had to see his baby boy in action.

 

And man he was not disappointed. Stiles was getting fucked like a proper whore, and not just for Derek. He was fucking nearly the entire pack, and in very kinky ways. And John saw it all. He saw how the Alpha would pound Stiles relentless against nearly every surface in the house. He saw Jackson fuck him as well while Lydia dictated. Even Scott was in on it, though he was considerably more gentle with Stiles. It made John smile to see the best friends so close, and now in such an intimate way.

 

But without a doubt, John’s favorite to watch was Peter. He loved when that deranged wolf visited and would make Stiles dress up in girl’s outfits. He loved that Peter had a thing for fucking Stiles in John’s office, or his bathroom, and even on bed. Watching his son getting the stuffing fucked out of him on the bed where he slept was like a perfect slice of pervert heaven for John. Now he made sure to time his return home so closely to Peter’s departure so that Stiles wouldn’t have enough time to change his father’s bed sheets. John would grip his cock in his hand so tight, cumming hard at the thought that he was lying in a mixture of Stiles’ and Peter’s juices. It was heady, and euphoric, but it was becoming less than enough for him. Standing next to his son the morning after he watched his hole getting pummeled by large werewolf cocks once used to fill John with a devious thrill. He loved to hold Stiles, discretely smell him, and when the teen was in the shower, sneak into his bedroom and blow his load all over his son’s pillows. But as he now sat behind his desk watching Derek and Peter tag team Stiles, both forcing their massive cocks inside his son’s tiny little fuckhole, he’d had enough.

 

John left the station before his shift was over. He passed Derek and Peter in Derek’s car as they drove down the street, and waved at them. He parked in the driveway and slipped into the house, removing his coat, shoes, and gun as he made his way to Stiles. He’d been furiously jacking his cock in the cruiser on the ride home and was two seconds away from orgasm. In fact, when he saw his son still lying on his side naked above the sheets, too fucked out to clean himself of the wolves’ cum that covered his backside and chest, John erupted. He blew his entire load all over Stiles’ sleeping face, shuddering in absolute pleasure when some of the creamy white fluid spilled into his son’s mouth.

 

Stiles slowly woke up when he felt something splash on his face, instantly moaning when he tasted salty cum on his tongue. But when he couldn’t discern who that delicious tasting cum belonged to, he opened his eyes fully and was met with his flushed and extremely aroused father.

 

“Daddy?”

 

That one word, moaned in such an innocent way, made John’s cock come alive again and even harder than before. He wrapped a hand around his member, moaning himself as Stiles watched. “Daddy,” Stiles asked again, but this time the innocence was gone, replaced by a seductive grin. His whore of a son said it just like the slut he is when he calls Peter daddy. And he said it as he licked some of his father’s cum from his lips.

 

It drove John wild.

 

“Please,” he asked, his voice cracked and suddenly unable to fully form a proper question.

 

But Stiles knew what the unasked question was. He ignored it for now. “Derek found the cameras weeks ago. You like watching your baby boy getting fucked daddy? I came so hard when Derek pounded me that night, knowing that I was performing for my own father. Do you like watching your son’s ass get brutally fucked by werewolves? Do you like how much of a cum slut I am daddy?”

 

Stiles ran a finger over the corners of his mouth, gathering up John’s cum and sucking his covered finger into his mouth. “Why do you think Peter and I fuck in your room more often? He loves to whisper in my ear how much of a slut I am for craving my real father. How disgusting I am for it.”

 

“S-stiles..please,” he begged.

 

Stiles smiled encouragingly at his father and decided to spare him from further torment. Falling onto to his back, he opened his long legs wide, pulling them up to his chest. “Come fuck me daddy. Let me take care of you.”

 

**FIN**

**Notes for the Chapter:**

> The Journey is over! If you decided to read this chapter, then thank you for being okay with the John/Stiles pairing. This was the FIRST and probably only time that i will write those two together. It wasn't the easiest thing to write, but this chapter was just as much fun as the others for me surprisingly. I can not believe that this took me over a year to complete, but thank you so much for sticking with me. I hope you enjoyed everything!
> 
> Much love  
> -CM


	11. The Best Plans Are Made Mid-Fuck

**Notes for the Chapter:**

> Hey Ya'll,
> 
> So sentineljandb suggested that I write a chappie to explain how Peter and Derek ended up sharing Stiles: 
> 
> It would be super hot, to read how Peter and Derek ended up sharing Stiles. Especially if they did it to get Stiles his wish, of getting together with his father. Did they suggest it, or was it Stiles's idea?
> 
> So naturally, I couldn't leave the idea alone and I wrote the chappie! LOL
> 
> Please don't flame me if it's complete shite. I am SOO exhausted ya'll. Acting isn't easy. Speaking as of which, I have a short film to go prepare for, so see you later peeps!
> 
> And as always, I luv you all!!!! <3 <3 <3

11

 

Derek, Peter, and Stiles were currently in John’s room, fucking like wild animals on his bed. It was actually Peter’s day to be alone with Stiles, but somehow Derek forgot and came over thinking that he would get the teen to himself. Seeing Stiles all dolled up in his schoolgirl outfit made Derek pop a boner real quick, and because he was technically both Stiles and Peter’s alpha, he demanded that he fuck Stiles as well. Peter didn’t care either way. The more the merrier. Currently they were all tangled together sandwich style with Peter below the teen and Derek above. Both wolves had their cocks shoved deep in Stiles’ tight little hole, but they took turns thrusting in and out so as not to overwhelm the human, and Stiles was happily never without a cock inside him.

“Fuck, Peter. You make Stiles dress up like a girl whenever you fuck him?”

Peter looked up at Derek over Stiles’ shoulder. “Yup. Brilliant isn’t it?”

Derek thrust in roughly. Stiles moaned loudly and Peter groaned from the feel of Derek’s sliding against his. He smirked down at his uncle. “Fuck yes.”

“My thoughts exactly. Right Genna?”

“Yes daddy,” the teen panted.

Derek raised a brow. “Genna?”

Peter shrugged and thrust up hard enough to startle Stiles, who in turn pushed back harder onto Derek’s cock, making the alpha toss his head back in pleasure. “What can I say? The kid loves being in character. Right baby? You like dressing up like daddy’s little slut? Like having two hard cocks fucking your tight little cunt? Like when daddy shares your greedy little pussy with his special friend?” Peter growled in Stiles’ ear.

“Yes daddy,” the teen said again when Peter pinched his nipples through his shirt. Peter liked it when he kept his clothes on, exposing only his hole underneath his plaid skirt. “See what I mean? But the ‘daddy’ thing was his idea though,” Peter said to his nephew. “Can’t imagine where that came from,” he said sarcastically.

Derek gave ‘Genna’ a hard slap on his ass. The bright red imprint that it left behind was so beautiful to Derek that he did the same thing on the other cheek. Stiles cried out, his lashes wet with unshed tears, his mouth open in ecstasy as he pushed back harder onto their cocks. Poor Stiles wouldn’t be able to sit straight for a week. “Probably has a thing for his real daddy. Is that it? Do you get your rocks off pretending that Peter’s cock is our favorite Sheriff’s? I wonder how deep that kink runs. Do you touch yourself at night, thinking about your father when he’s in the next room? Do you dream about being his wife? A good, perfect little wife who opens up her legs to welcome him home from work? Or when you think about sitting on his cock, are you his innocent baby boy? Huh? Does the baby boy want to get bred by his daddy?”

Stiles didn’t say anything to Derek’s taunting, his pink glossed lips pressed into a thin line.

Peter chuckled. “Aww now’s not the time to stay quiet baby. You don’t have to be shy around us, _especially_ us. We understand those kinds of needs, right Derek?”

Derek grinned and leaned down, placing a biting kiss on Peter’s lips so rough that his teeth broke the skin. But that seemed to spur them on even more, and Stiles whimpered as he watched the two wolves go at it, both fighting for dominance with teeth and tongues, but Derek eventually won out. He pulled back a bit, nipping the soft flesh of Stiles’ earlobe. They both watched as Peter sensuously licked the remaining trace of blood from his lips, eyes flashing blue before they returned to their normal brown. “Something about his crazy ass is quite appealing,” Derek growled in the teen’s ear. He slammed in brutally, making both Peter and Stiles moan from the surprise of it. “So we know all about secret desires _Genna_.”

“And we’ll help you get our beloved Sheriff into bed if you want, even though I’m sure it won’t be too difficult,” Peter said, pointing to a glowing red light coming from the corner on the ceiling. Derek nodded. “There’s one in your bedroom too Stiles, near the closet. I saw it weeks ago.”

“I think daddy dearest already suspects what his baby boy is doing. Maybe he likes it. I know I would,” Peter said in a sing-song way.

“You’re a fucking pervert Peter. You too Derek,” Stiles added afterwards. “Beginning to think the apple doesn’t fall far,” he huffed, but smiled at the idea all the same.

“Guilty,” the older wolf said with a huge grin.

“Same. Sooo… maybe we should plan something and find out. Wouldn’t want daddy Stilinski missing out on all the fun,” said Derek with a dark grin. He signaled to Peter and they began their pace anew, pounding Stiles’ hole so hard that the teen came with a shout moments later, ropes of white cum catching on the pleats of his skirt and Peter’s chest.

“Yeah okay,” Stiles agreed and collapsed on top of Peter completely, fully relaxed and boneless. He lay there more than content to let both wolves use his hole for their pleasure while his mind drifted to his father and how many different ways he could persuade the older man to fuck him.

 

So many, many ways indeed… ;)

 

**Notes for the Chapter:**

> Oh yeah, if you have ideas for future chapters to this fic, please leave 'em in the comments below. I can't promise that I'll write them all, or that I can do any of them in a timely fashion (took me over three months for this one, lol), but I can most certainly try. :D
> 
> -CM


	12. After School Special

**Notes for the Chapter:**

> This takes place after chapter seven: "Lydia watching us fuck is really kinda hot."  
> This idea wouldn't leave me alone, and really, who doesn't want more Stackson? ;)
> 
> Enjoy!
> 
> Un-beta'd
> 
> New Tags Added: Rimming, Locker Room Sex, Werewolf Healing

12

 

Jackson waited until everyone had left the locker room before he cornered Stiles in the shower. He had seen the pale teen limping during practice, and he wanted to apologize to him. The night before had been something else. With Lydia in the room, commanding his every movement, Jackson went a little crazy. His dick had never been that hard before in his life, and the need to get off was damn near blinding. He remembered unleashing everything he had on Stiles and not really stopping to think if the boy could handle all of it. As he watched Stiles limp into the showers and step under the spray of the water, Jackson had his answer.

But he didn’t walk over to Stiles just yet. Instead he watched from the shadows for a few minutes, eyes glued to the soapy suds that covered every inch of that pale skin. He watched as Stiles lathered up his hands and ran them over his arms and chest, and then repeated the routine with his thighs and legs. Jackson had to adjust his dick in his shorts when Stiles ran those long fingers of his over his cock, giving it a few quick tugs before moving onto his balls hanging heavy underneath.

Even though Stiles was completely unaware that someone was watching him shower, the scene before Jackson was pretty erotic. Stiles wasn’t doing anything particularly sexy—he was just washing himself as he would on any other day. He wasn’t playing with his nipples or stroking his cock. In fact at the moment, he was washing his hair and humming the theme song to Elmo’s World. _Maybe Stilinski is just naturally sexy_ , Jackson mused. Of course he thought that just as Stiles broke out into some weird techno beat and started doing the robot. _Maybe not._

Nonetheless, Jackson couldn’t deny that he was drawn to the other boy in ways that he wasn’t previously. Obviously they were pack, even though Stilinski was still human. But maybe they were more—maybe he even thought of the two of them as friends now. Whatever the case may be, he had caused his packmate some pain, and now he wanted to make up for it.

The sound of Stiles hissing tore Jackson away from his thoughts. The other boy had stopped dancing (flailing, because what Stiles was doing most certainly wasn’t dancing), and was currently holding his plump cheeks apart. A lone index finger was probing at his tender entrance, and even from where Jackson was standing, he could see that Stiles was really sore.

“Ouch,” Jackson said as he stepped from the shadows and into the light.

Startled, Stiles turned to face the intruder and shielded his privates on instinct. When he noticed who it was, he relaxed and dropped his hands, turning back to the water. “Did you need something Jackson?”

“I just came to check on you. Rough night last night,” he said amusedly.

Stiles snorted. “Why? Afraid you fucked me too hard?”

“Actually, yeah.”

Stiles snorted again. Jackson rolled his eyes. “And I also came to apologize. I didn’t realize that she was going to be like…that,” he finished lamely.

Stiles looked over his shoulder at Jackson, raking his eyes up and down the athlete’s body. Jackson was nearly naked save for his shorts that had an interesting tent in the front. In the end, he shrugged and washed the remainder of shampoo from his hair. “Last night was fine. And Lydia is Lydia. I found the whole thing to be hot even though I was practically afraid for the safety of my nuts at one point.”

Jackson smiled and dropped his shorts, stepping into the shower behind Stiles. He wrapped his arms around the boy’s tiny waist, resting his head on a freckled shoulder. “She wouldn’t have done anything to hurt ya. I wouldn’t have let her,” he said as he sucked and bit at a patch of skin on Stiles’ neck. It turned dark and bruised in a matter of moments.

Stiles arched his neck to give the boy better access. “Are you here for round two Jay? Although you should know better. Today isn’t your day to have me. And your girlfriend might not appreciate that.”

Jackson laughed. “Yeah Lydia might be a bit of a bitch, but whatever right? She’s not here to complain and no one has to tell her anything,” he said, pulling Stiles close. “I really like fucking you Stiles. I like that even though you fuck all of the other guys in the pack, you still get so tight for me.”

“Fuck Jackson,” Stiles sighed, rubbing his ass against the captain’s growing hardness.

“But I hate that I left you like this. Everyone on the team noticed today. Even coach. And McCall glared at me the entire time. Made me feel like a total douche.”

“You should have just ignored them. And besides, I like it when you guys get particularly rough with me. Leaves me with something to remember until the next packmate shows up.”

Jackson stroked his sides. “Does that mean that we can never be gentle?” He kissed his way up Stiles’ neck, pulling the flesh of Stiles’ earlobe between his teeth and nipping at it softly. “Never ever?”

Stiles stammered for words. “N-no gentle is good. Gentle is great.”

Jackson chuckled. “Good.” He promptly dropped to his knees, exposing Stiles’ hole to his greedy eyes. It was puckered and loose, pulsating under his gaze. Winking at him invitingly. He squeezed Stiles’ ass cheeks harder, pulling them wider apart until he could see the tantalizing pink flesh inside. He ran the tip of his tongue around the angry red rim, spurred on by Stiles’ moaning.

“Feels so good Jackson. Need more. Give me more. Please,” Stiles whimpered, sighing when he got his wish and Jackson eased his tongue inside his aching hole, fucking him nice and slow. As he did so, black veins formed on his arms, effectively absorbing Stiles’ pain until there was none left.

“You taste so good baby,” Jackson growled. “I could fucking lick you out all the time. Would you like that baby? Want me to eat out your little pussy whenever you want?” He blew on that spit-slicked hole, watching in delight when it winked at him.

Stiles moaned and nodded, pushing his ass back into Jackson’s face. “Yeah Jay. Tongue fuck my pussy all the time.” Stiles panted against the tile, dick fully hard and throbbing. “Harder. Need it harder. Need to cum. Please let me cum.” He tried to touch himself but Jackson wouldn’t let him, ordering him to keep his hands flat against the wall. He pushed Stiles forward so that his front was flat against the wall. Stiles damn near howled when his hard cock made contact with the cool surface, jolts of electricity shooting down his spine when Jackson maneuvered him so his cock rubbed against the porcelain. The jock thrust his tongue in at a rapid rate, growling when Stiles clenched around him, the overstimulation forcing the teen to shut his legs from Jackson’s torment. But Jackson held him open, using his strength to pick Stiles off of the ground. The teen gasped when he felt the floor disappear from under his feet, arms flailing around for anything to hold onto. Eventually he realized that Jackson was holding him up, pushing and pulling him back onto his tongue like a doll. Like he was a weightless fuckdoll. The end result was that Stiles was in fucking heaven as he let Jackson manhandle him, let him spear him open and force him through that delicious onslaught.

A few moments of that and Stiles felt his balls tighten, his dick flopping in the air. “Oh god, I’m gonna cum Jay.”

“Yeah? Gonna cum on my tongue? Go ahead baby. Cum for me.”

“Fuck Jay,” Stiles groaned, going completely rigid as he came untouched, splashing the walls with ropes of cum.

He almost slid down to the floor when Jackson placed him back on his feet. Luckily the captain kept an arm around his waist. Instead, Stiles was bent over and his feet were kicked wide apart. In that position he was forced to bare his hole again. With a few quick pumps, Jackson aimed his cock at that fucked out hole, painting it in streams of white. He slapped his cock against that hole, squeezing any remaining drops that he had left.

After a few minutes, Jackson righted Stiles in his arms, maneuvering them both so they stood under the spray of the hot water. Stiles glanced down at their feet, tutting when Jackson’s seed washed away down the drain.

“It’s a shame all that perfectly good cum went to waste.”

Jackson placed a kiss behind his ear. “Don’t worry. I’ll give you a nice warm load in the future. When it’s technically my day.”

 

**FIN**

 

How was it? I hope my Stackson fans enjoyed it. I sure had fun writing it!

~~Also, one of my readers suggested a lovely idea for a future chapter: Stiles vs. a fucking machine. But who will man the control? Ladies and Gentlemen, I might just be able to give you a Stiles/Isaac chappie after all! ;)~~

~~Until then, much love peeps! :)~~

~~-CM~~

**UPDATE (1/21/16): Due to a recent incident, I will no longer add any additional chapters to this story.**

**-CM**


	13. Ruby Woo

**Notes for the Chapter:**

> Hi guys, so after much internal deliberation, I have decided to continue on with this kink fic and finally get to my Stisaac chappies. FYI: my reason behind having Isaac being mentioned this late into the fic is that he was abroad in Japan. Just go with it and enjoy, lol. 
> 
> -CM
> 
> Warning, New Kinks Added: Slight Cock Wrapping, Lipstick

 

Stiles opened his locker, and sighed as he placed his science textbook inside. Mr. Harris was being more of a dick today than usual. He probably hadn’t been laid in like…forever. Not that Stiles could relate.  He’s surprised his hole doesn’t whistle every time a breeze happens to pass by with all the sex he’s been getting. Not that he’s complaining. Nope, far from it. In fact, he recently discovered that he can’t stand being empty for long periods of time. Sitting through class everyday is like torture for him, especially when he knows that he has at least four willing cocks that he can sit on instead of a hard wooden desk chair.

Scott, whose locker was right next to Stiles, heard him sigh and frowned. “You okay baby?” he whispered.

Stiles raised an eyebrow at the nickname, but flashed his best friend a big smile. “Yeah Scotty, I’m fine. Trying to shake off the last 60 minutes of Mr. Harris’ bullshit.”

“You sure? I heard you’ve been pretty busy lately,” Scott began, stepping closer to the pale teen when no one was looking. “Gang banged by the Hales. Riding your own father’s cock. You gotta be a bit sore.”

Stiles moaned at Scott’s words, aware enough of his surroundings to do so quietly. But there was barely anyone left in the hall and that allowed the werewolf teen to run his hand down Stiles’ back all the way down to the swell of his ass. He squeezed one of the plump cheeks, causing Stiles to squeak and swat at his chest. “Kiss me,” Scott whispered against his lips. Stiles gave a quick look around before obliging, sighing into the warm embrace when he felt Scott absorbing away his lingering soreness.

“I can’t wait til I’m inside you again baby,” said Scott. “Maybe I should take you right now where we might get caught. Or maybe on Mr. Harris’ desk before his next class. Would you like that Stiles?”

“You know I would.”

Scott chuckled. “I bet. Too bad it isn’t my day,” he said with a smirk as he stepped away. He laughed when Stiles protested and pointed to his raging boner. “Sorry buddy, but I can’t do anything about that til  Friday. And its Monday, so….”

“I hate you,” Stiles grumbled, but without any heat. He trudged along behind Scott as they made their way into the cafeteria. They grabbed their lunch and made their way over to their usual table  where they met a bored Jackson who perked up slightly when Stiles approached, an even more bored Lydia on her phone and didn’t care who approached, and…Isaac.

“Isaac! When did you get back from Japan, dude?” asked Scott. He took a seat next to Jackson, and Stiles sat next to the newcomer, placing his backpack on the floor between them.

“Last night,” the brunet replied.   He toyed around with his mashed potatoes in silence. That was Isaac, man of a few words. And he looked good, Stiles reason. Still a bit broody, but handsome as ever.

“And in the middle of a semester at that,” said Stiles. When Isaac’s eyes locked on his, a shiver ran down his spine. His eyes were just so intense, as if he were peering straight through him. Stiles wiggled in his seat and unwrapped his sandwich. When he couldn’t get the ribbon on his sandwich untied, Isaac reached over with a clawed index finger and shredded the sting with ease.

“Thanks,” said Stiles with a bashful smile.

“No problem,” Isaac replied. “And yeah, it wasn’t that hard to reintegrate into the whole high school saga. I’ve been emailing with my teachers since the start of the school year, taking tests and passing in homework online. So getting back into the swing of things wasn’t difficult,” Isaac said with a shrug.

“Well that’s good. Still, we’re pretty close to midterms so if you need to look at my notes just let me know and we can set up a study session.”

“Thanks Stiles. I’d like that.”

Later on when Stiles was home and going through his backpack, he came across something odd. A small black cylinder mixed in with his pencils and highlighters.

MAC No. B51 Ruby Woo red lipstick.

It was an odd sight to see and something that was definitely not his. He opened it. It was a brand new tube, and decidedly a pretty shade of red. Sultry, sexy, seductive. Well that settled it; it had to be Lydia’s. Somehow it must have fallen into Stiles’ bag. He set it on his nightstand so that he wouldn't forget to take it with him in the morning.

“Ah the joys of Trig,” he mumbled, picking up his math textbook.

 

*****

 

Stiles woke up feeling weird. Well not really weird per se, but relaxed. Like reeeally relaxed. Muscles were a pile of goo, spine was non-existent. It felt  just the same as having a system overloading orgasm, but Stiles knew he hadn’t had one of _those_ in a few nights.  And he didn’t remember having a good dream, so he’s not sure where the feeling was coming from.

Stiles stretched and move to pull he sheets back…only to realize that he wasn’t under the sheets, but on top of them. And he was naked. Deliciously naked.

Stiles grinned. One of his pack mates paid him a visit last night. How exciting. Judging by the style, he assumed this was Peter’s doing. Peter had the tendency to perfect every finite detail, and make everything single thing count. And this wolf definitely followed along similar lines. But it couldn’t be Peter or Derek for that matter because both Hale men were off conducting pack business in the next town over. And unless Jackson escaped from the clutches of Lydia’s mandatory bonding time, it wasn’t him either.

So Scotty boy it was. And with him trying to sex Stiles up in the hall way earlier, that would make sense.

Except when Stiles stood up and walked over to his floor length mirror, the evidence proved contradictory. Spanning from the underside of his chin down to his ankles were red lipstick kisses. Around his cock was a thick, purple ribbon made of the highest quality silk. It winded gently down the shaft of his cock and around his balls, forming into the neatest bow around the base like a perfectly wrapped present.

Stiles touched every inch of his skin. No, this wasn’t Scott. This was different, exhilarating. This was new. He ran the tips of his fingers across the only word written on his body, imprinted in delicate red script across the expanse of his abdomen.  Written in whatever was left of the tube of lipstick now open on his nightstand.

**_Soon._ **

He smiled. “Okay.”

 

**TBC…**


	14. Deus Ex Machina

**Notes for the Chapter:**

> WARNING- New Tags Added: Feathers, Ice cubes, Japanese silk rope, Shibari rope style bondage, sex machine, blindfolds, NSFW ART
> 
> Dedicated to Panda_Blitz
> 
> Enjoy!
> 
> -CM
> 
> P.S. I'm starting a new series. Read about it in the notes section below.

_“Hey Stiles, wait up!”_

_Stiles turned around to see Isaac sprinting up to him. They just had homeroom together, and because their only other shared class was Mr. Harris’s, Stiles was on his way across the school for his Trig class with Scott. He gave a small smile and a head nod to his best friend, signaling that Scott could go on without him._

_“Hey,” he said when Isaac caught up._

_“Hey,” said Isaac. For a few seconds they were just staring at each other while their classmates filed out around them. “I was hoping I could take you up on your offer from yesterday,” Isaac said when they were the only ones left in that part of the hallway. “Even though I’ve been keeping up with the class, I think I might need to cram in a few hours of studying before Friday’s exam. Would you be able to swing over my house tonight?”_

_Stiles nodded. “Sure, of course! The bookwormy nerd in me is always ready to help out a fellow student in need.”_

_Isaac cocked his head, and fixed the pale teen with a look that he couldn’t interpret. It was heavy, and made him shift from foot to foot as his neck grew hot. He adjusted his backpack on his shoulder, but in doing so he dropped one of the books in his hand. Immediately he bent down to get it, but Isaac did as well and got to it first._

_The werewolf teen handed it over with a rare smile. “Thanks Stiles. I’m sure there’s a lot I’ll learn from you tonight.” He walked away without another word, leaving Stiles behind with scarlet colored cheeks._

_*****_

 

Stiles whimpered, the sound itself small but amplified over the general silence in the room. He subconsciously tugged at the rope bindings around his hands, but the intent wasn’t to escape them. No, he liked being bound—like to remember that the rope was there, keeping him from moving away from his sensual tormentor. The whole situation made his cock impossibly hard, but the silk ribbon around his cock and balls prevented him from cumming.

He heard movement to his right, and seconds afterward felt a something soft connect with his abdomen. He couldn’t tell what it was because he was blindfolded, but if he had to guess based on the texture of the item, Stiles would guess it was a feather.

“Do you know why I went to Japan Stiles?”

The pale teen twitched when the feather brushed against his ticklish ribcage. “To st-study abroad?”

A chuckle emerged. “During the school year? Come on Stiles, you’re smarter than that.”

Stiles moaned when the feather brushed over his nipples. “I figured it was werewolf related.”

The feather disappeared from his skin for a moment. In the silence, Stiles couldn’t pinpoint Isaac’s location. He jumped when the wolf’s voice sounded next to his left ear.

“After the whole situation regarding my father’s death, I thought it was best that I escape Beacon Hills for a bit. Japan seemed like the best place to go. I spoke to the Hales about it and they agreed. Plus Peter has a friend, a shaman, out there who offered to take me in for a few months.” The feather reappeared. “It really is a wonderful place. Peaceful. The language, the culture, the people are all fascinating and there’s so much to learn,” Isaac murmured, dragging the feather around Stiles’ bellybutton, sniggering as the pale teen’s abdomen fluttered under the sensation.

“The Shaman taught me not only how to calm my rage and control my wolf during the nights of the full moon, but how to manage it by channeling it’s power into other outlets. Some people choose to find their mental calm through yoga and meditation. I discovered my outlet to be of a more sexual nature,” Isaac purred.

Suddenly the feather was gone altogether, replaced by something more solid and much, _much_ colder. 

Stiles gasped as the ice cube slid up his abdomen and connected with his right nipple. It circled around it repeatedly, hardening the rosy bud into a stiff peak. “A werewolf is a highly sexual creature, as I’m sure you’ve well experienced by now. I could smell them on you, in you. I imagined them taking you many times, fucking you like a two-bit whore. I bet you moaned for them like one.”

“Isaac,” Stiles whined, fidgeting. The coldness of the cube was intense, stinging just enough to hurt.

“You’ll moan for me too Stiles. But you’ll find that my wolf will be pleased by you in a different way,” the werewolf replied with a slight growl. He replaced the ice cube with his mouth, smiling in mirth as Stiles screamed, back arching off the bed like a tightly strung bow.

 

*****

_The torture continued on for many moments, tears forming in the corner of Stiles’ eyes as he was brought to the brink of icy pain only to be relieved by the suction of a burning mouth. It was delicious. It was intoxicating being tied up and blindfolded and left to the mercy of a wolf. It had every one of Stiles’ nerves standing on end. And then he was being moved—rearranged into a different position on a chair this time. The ribbon around his cock came off with a slight tug. The silk ropes that were wound around his body were being fastened a in different way so that his bound hands were now behind his head. He was brought to the edge of the seat, and each leg was placed over each arm of the chair, his cheeks now involuntarily parted and his hole thoroughly exposed._

_The blindfold was also removed, and when his vision cleared, Stiles found Isaac placing a vinyl record on an old phonograph across the room. There was a pot of tea and cup on a small table nearby, the steam from the teapot wafting up into the air. Soft opera music filled the room, an aria that Stiles scarcely recognized. Samson et Dahlia, Carmen, Rigoletto…it was one of those. Stiles was having a hard time forming a thought. Sitting in the chair so exposed, his hole practically begging for a hard pounding but being utterly ignored by his tempter was making Stiles so horny that he could barely think straight. If he could get free from his bindings he didn’t know if he would hurt Isaac for all of this insane foreplay, or yank his pants down and ride his cock until sunup._

_He was about to say something—to complain, but then Isaac turned to face him with a single flower in hand.  “I have a gift for you,” the werewolf teen said, gliding over to his prey. He ran the flower up the length of Stiles’ cock, letting the petals linger on the reddened bulbous head. They soaked up the precum pooling there like a sponge, and when Isaac pulled the blossom away, a thin trail of precum followed._

_ _

_“Like fresh dew on a beautiful spring morning after a gentle rain.” Isaac brushed the flower over his lips. Stiles whimpered when he saw his pink tongue emerge to lick the glistening fluid from his lips. “Divine,” Isaac purred, savoring the taste. He placed the flower by the teapot afterwards and went over to his closet._

_“And now for your gift,” he said, wheeling out a small cart. Whatever was on it was covered with a black cloth. Isaac pushed the cart over until rested between Stiles’ open legs._

_And then he removed the cloth._

 

*****

 

“Fuck Isaac,” Stiles panted over the tune of the music and the slight buzzing noise of the fucking machine.

The blonde bastard just glanced at him with an observatory look before reaching for the teapot to replenish his cup. If it weren’t for the bulge in his trousers, Stiles would think this whole night was a weird social experiment. But it seemed like Isaac was enjoying the scene before him quite a bit, even though on the outside he appeared calm and collected. He looked like the epitome of a GQ model, sitting on the plush armchair across from him in a wine-colored button down shirt and black trousers. His shoes were polished, and his watch glinted in the soft light. He took a sip from his cup. It was like Isaac was a guest watching the most entrancing performance unfold before him.

Meanwhile, Stiles was moaning like the whore of Babylon as the thick flesh-like dildo thrust into him at a leisurely pace.

“Enjoying yourself?” Isaac asked bemusedly.

Stiles threw him a glare, but moaned when the dildo went deeper and pressed against his prostate. “I should ask you the same thing. Is this how you get your rocks off? Tying people up and watching them get fucked with your machine?”

Isaac quirked an eyebrow. “People? Oh no, Stiles. I built this little device all for you. Everything is all for you.” He put down the cup and picked up the small remote on the table. “You have no idea how beautiful you look right now,” Isaac whispered. “How beautiful your hole looks stretched around that fake cock.” He pushed a button on the remote, smiling when Stiles gasped at the new punishing pace of the machine. It fucked him so hard and deep and fast, pummeling his hole with a speed that no human could match. And then Isaac pushed another button and Stiles squeaked and clenched his eyes shut as the dildo started vibrating as it moved in and out of him.

Stiles knew the end was near; could feel his balls tighten with every thrust. Could feel his whole body pulsate from the vibrations. His toes were curled so taut that it would take hours before the muscles would relax again. He tried to withstanding the building heat in his belly, tried to last just a bit longer. But in the end he couldn’t, and holding the gaze of his teasing lover he cried out as he came, ropes of white erupting like a volcano all over his chest and thighs.

A button was pushed.

The buzzing stopped and the dildo stilled inside of him.

The last song on the phonograph came to an end.

“Fuck,” Stiles sighed as he tried to regulate his breathing. Cuming untouched and so hard always left him utterly breathless. Not that he was complaining. The whole experience was thrilling, and bizarre, and so erotic. He never thought he’d ever cum from a machine fucking him, and was pleased that Isaac had introduced him to this exotic kink.

Speaking of the werewolf, as he approached, Stiles fully believed that he was going to release him from his bindings. Instead, Isaac bent down so that his lips were level with Stiles’ ear. “So beautiful.”

The pale teen groaned and tugged at the rope around his hands. “Isaac let me take care of you now. You’ve been hard for so long. Don’t you want me to take care of you?”

Isaac pressed a kiss to the shell of Stiles’ ear. “So eager to help. Like a puppy that’s desperate to show its master affection. I adore you Stiles,” he said with a chuckle. “But no, you’re going to stay right where you are, and I’m going to turn the machine on again and finish my tea. I might even watch a movie or read a book or two.” He ran his finger through the cooling cum on Stiles’ belly, licking it off his finger with a wet plop. “You’re going to get fucked again, and again, and again Stiles, until you’ve cum so many times that your balls are drained and you’ve forgotten your own name. And when you’re delirious from your multiple orgasms, and you can’t form proper words, I will carry you back to my bed and unwrap you like the beautiful present that you are. I’ll massage every kink from your sore limbs, and lick every salty tear that streaks across your face. I’ll praise every inch of you with soft words and even softer kisses.  And just as you begin to drift off into dreamland, I’m going to pull my cock out and paint your face with my cum.” He stood up then and gave a small pat to Stiles’ shoulder. “Sound good?”

“Yes,” Stiles breathed, his cock already hardening with every word.

Isaac flashed him a dazzling smile. “Good boy.”

**TBC…**

**Notes for the Chapter:**

> How was it? I hope you enjoyed this LONG awaited chapter. The image btw is not mine at all, nor is it Teen Wolf related. I just happened to see it and thought that it fit the nature of this chappie perfectly. Credit goes fully to Yaoinmylife on Tumblr.
> 
> Next chapter is the final chapter, and will be dedicated to OrdinaryMortal. They wanted to see a flashbackish type chappie where the pack talks about Stiles becoming their pack slut, and I am happy to oblige. Wish granted my friend. ;)
> 
> Also, sentineljandb inspired a new series in me, a Briar Derek drabble series. It will be shorter than this one but just as fun as we explore how Derek and crazy uncle Pete started having sex. I will warn ahead that Derek will be quite young in that series when they start, probably 13 or so, and the age gap btwn him an Peter will be wider than in the show. I hope to start that one up soon.
> 
> Much Love Peeps,
> 
> CM


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